34441-14-0
Chemical Structure
Nicotianamine
- CAS No.: 34441-14-0
- Formula:C12H21N3O6
- Molecular Weight:303.31
IUPAC Name: (S)-1-((S)-3-(((S)-3-amino-3-carboxypropyl)amino)-3-carboxypropyl)azetidine-2-carboxylic acid
InChIKey: KRGPXXHMOXVMMM-CIUDSAMLSA-N
SMILES: OC([C@@H](N)CCN[C@H](C(O)=O)CCN1[C@@H](CC1)C(O)=O)=O
Biological Activity: Nicotianamine is an orally active ACE inhibitor with an IC50 of 76 nM for rhACE2 and an IC50 of 59 nM for rhACE. Nicotianamine is also a metal chelator with high affinity for ferrous ions and other divalent metal cations. Nicotianamine is isolated from soybean. Nicotianamine reduces systolic blood pressure in spontaneously hypertensive rats. Nicotianamine chelates iron and zinc, promotes iron transport, enhances iron bioavailability through stable Fe2+-NA complexes and intestinal Fe2+ uptake, and promotes phloem-to-sink Fe mobilization, long-distance transport of Zn to leaves and flowers, and pollen development. Nicotianamine is a biosynthetic precursor of plant phytosiderophores, reverses chlorosis, and rescues sterility in NA-free mutants. Nicotianamine is used in research on hypertension, chlorosis, and iron deficiency anemia[1][2][3][4][5][6].
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Nicotianamine | Nicotianamine is an orally active ACE inhibitor with an IC50 of 76 nM for rhACE2 and an IC50 of 59 nM for rhACE. Nicotianamine is also a metal chelator with high affinity for ferrous ions and other divalent metal cations. Nicotianamine is isolated from soybean. Nicotianamine reduces systolic blood pressure in spontaneously hypertensive rats. Nicotianamine chelates iron and zinc, promotes iron transport, enhances iron bioavailability through stable Fe2+-NA complexes and intestinal Fe2+ uptake, and promotes phloem-to-sink Fe mobilization, long-distance transport of Zn to leaves and flowers, and pollen development. Nicotianamine is a biosynthetic precursor of plant phytosiderophores, reverses chlorosis, and rescues sterility in NA-free mutants. Nicotianamine is used in research on hypertension, chlorosis, and iron deficiency anemia. | |||||||||||||||||||||
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References
- [1]. Takahashi S, et al. Nicotianamine is a novel angiotensin-converting enzyme 2 inhibitor in soybean. Biomedical research (Tokyo, Japan). 2015;36(3):219-24. [Content Brief]
- [2]. Kataoka S, et al. Functional effects of Japanese style fermented soy sauce (shoyu) and its components. Journal of bioscience and bioengineering. 2005 Sep;100(3):227-34.
- [3]. Takenaka T, Murayama T, Furusho T, et al. Antihypertensive effects of nicotianamine from soybean broth in spontaneously hypertensive rats[J]. Food Science and Technology Research, 2009, 15(5): 541-546.
- [4]. Bouazaoui M, et al. Synthesis and biological activity of nicotianamine and analogues. Adv Exp Med Biol. 2009;611:555-7. [Content Brief]
- [5]. Beasley JT, et al. Investigation of Nicotianamine and 2' Deoxymugineic Acid as Enhancers of Iron Bioavailability in Caco-2 Cells. Nutrients. 2019 Jun 30;11(7):1502.
- [6]. Schuler M, et al. Nicotianamine functions in the Phloem-based transport of iron to sink organs, in pollen development and pollen tube growth in Arabidopsis. The Plant cell. 2012 Jun;24(6):2380-400.
